Dakota Skye stops by to talk to her friend's brother, Preston. She needs guy advice. She wants to have sex with her new boyfriend but she has never done it before and she is scared of getting pregnant. Preston suggests she have anal sex to avoid the risk of pregnancy. Dakota asks Preston if he can show her how to take dick in the ass. After some convincing Preston agrees.

When Tyler walks into Julia Ann's classroom with lipstick all over his face Julia can't help but ask what he was up to the night before. Tyler lets her know about the frat he's trying to join and how he passed out at their party after drinking too much. Apparently, the frat boys had some hazing fun with Tyler and drew all over his face and he had no idea until Julia pointed it out. She takes pity on her student and helps him clean it off his face. Then she decides to make his day better by taking his cock in her pussy. If only all teacher's could be this caring.

Alura Jenson is a hot busty blonde sexuality teacher. Karlo seeks her advice since sex is her expertise. He hasn't been able to perform in bed lately. Alura can definitely help with that. She believes in the more hands on approach to teaching and boy does she get her hands on Karlo. Her big butt bouncing on his cock has him cumming in no time. Alura truly is an expert in her field.

"""Why not be a Playboy model?"" Ashley thought when she submitted her photos to our offices. ""You're only young once. My best friend said that I should send in my photos, so I did."" Ashley is a budding legal secretary?"

Playboy Plus is on set with Elizabeth Marxs to shoot her exclusive pictorial. Get to know more about Elizabeth Marxs by watching our behind the scenes footage and the complete nude version available exclusively on Pl?

Playboy Plus is on set with Brittany Evans to shoot her exclusive pictorial. Get to know more about Brittany Evans by watching our behind the scenes footage and the complete nude version available exclusively on Play?

Playboy Plus is on set with Jessica Renee to shoot her exclusive pictorial. Get to know more about Jessica Renee by watching our behind the scenes footage and the complete nude version available exclusively on Playbo?

Scarlet comes in and apologizes about being late. As she turns around she sees that it's her sister's ex-boyfriend Bill. She takes a look at his resume and mentions a qualification that isn't listed like how he sexually pleased her sister in bed. Scarlet grabs Bill by the tie and spreads open her legs and asks Bill if he really wants to the job. Who knew a desk job interview could be so physically exhausting.

Sandee Westgate has a new boyfriend. Her boyfriend has an adult son who just got in the night before and Sandee decides the best way to introduce herself is to head on over to his room in her sexiest lingerie and give him a morning blowjob . Of course her boyfriend's son is surprised to wake up to a hot women sucking on his cock, specially after he finds out that it's his dad's new girlfriend. Sandee really needs younger cock though and as soon as she pops her tits out her boyfriend's son calms all his fears about fucking his dad's hot girlfriend.

Riley Reid is a hot photographer who is taking some pics of her boyfriend's friend, Chad, as a favor. Riley is really artistic though and totally into the human body and wants to take some artistic nudes of Chad. Chad is a little hesitant as Riley is his friend's girl, but Riley is super convincing and gets his clothes off. Once the clothes come off there's something else Riley wants from Chad..his cock!

Bill gets home after a tiring day at work and his friend's girl, Audrey Bitoni, meets him in a sexy outfit. She's always wanted Bill and since her boyfriend is out she decided that it was the perfect time to make her move on him. Bill is reluctant since she is her best friend's girl, but all his reluctance goes away once Audrey pops her titties out.

GIRL WHO WEARS GLASSES librarian Virginia Gordon: special edition in a deluxe binding Playboy has garnered Playmates from many walks of life, but a whiskered old prejudice about the plainness of librarians, as we?

Playboy Plus is on set with Francessca DeMarco to shoot her exclusive pictorial. Get to know more about Francessca DeMarco by watching our behind the scenes footage and the complete nude version available exclusively?

Playboy Plus is on set with Kimber West to shoot her exclusive pictorial. Get to know more about Kimber West by watching our behind the scenes footage and the complete nude version available exclusively on Playboy Pl?

Playboy.com is on set with Gracie Lewis to shoot her exclusive pictorial. Get to know more about Gracie Lewis by watching our behind the scenes footage and the complete nude version available exclusively on Playbo?

Playboy.com is on set with Aurora Maria to shoot her exclusive pictorial. Get to know more about Aurora Maria by watching our behind the scenes footage and the complete nude version available exclusively on Playboy P?

Playboy Plus is on set with Janine Siu to shoot her exclusive pictorial. Get to know more about Janine Siu by watching our behind the scenes footage and the complete nude version available exclusively on Playboy Plus?

Summer Brielle needs sex advice so she visits the biggest porn connoisseur she knows, her boyfriend's best friend Ryan. Summer needs Ryan to give her sex tips to help surprise her boyfriend. She brings over toys so Ryan can give her advice. During the demonstration Summer gets a little to excited and decides it's time to stop playing with toys and start playing with the real thing. She seduces Ryan into fucking her brains out. He's a little hesitant at first, but once he takes a look at Summer's big tits he's all for fucking his friend's hot girl.

Scarlet Red is spending the night at her friend's place. Since her friend is busy fucking her boyfriend Scarlet ends up passing out on her friend's brother's bed. He gets home and finds her sleeping in nothing but her underwear. He convinces her to stay in bed with him. One thing leads to another and they're fucking in no time.

Raven Bay is making sure to stay groomed for her boyfriend by shaving her naughty bits, but she's doing so out on the veranda. Her boyfriend's son catches her and decides to confront her about it, but Raven knows that in reality it's turning him on. She can see his boner popping out through his jeans, so she throws him a bone and invites him to shave her pussy for her. As soon as he's done she let's him take a crack at stuffing her freshly shaved pussy with his cock. He obliges as he does have to relieve his boner...and they both promise not to tell daddy about their naughty experience together.

The beach is always special for Nina because she lost her virginity there. One day her boyfriend took her there at night and under the moonlight he destroyed her cooch and showed her how to swallow cum. It was a magical night!

Darla Crane is having her new boy toy over to her house, but when he arrives he's acting a little suspicious. She finds a wedding ring he's been trying to hide and he confesses that it's the anniversary of his ex-wife's passing and he was wearing the ring to commemorate her. Darla feels so bad for him that she gives him an extra special titty fuck before taking his hard cock in her wet and waiting pussy.

Playboy Plus is on set with Nikki Bishop to shoot her exclusive pictorial. Get to know more about Nikki Bishop by watching our behind the scenes footage and the complete nude version available exclusively on Playboy?

When Tyler walks into Julia Ann's classroom with lipstick all over his face Julia can't help but ask what he was up to the night before. Tyler lets her know about the frat he's trying to join and how he passed out at their party after drinking too much. Apparently, the frat boys had some hazing fun with Tyler and drew all over his face and he had no idea until Julia pointed it out. She takes pity on her student and helps him clean it off his face. Then she decides to make his day better by taking his cock in her pussy. If only all teacher's could be this caring.

My boyfriend loves my body! Especially my tits. ?Not too big and not too small but round and firm with those big, succulent nipples.? He spends plenty of time sucking on those luscious nipples. Of course he?s also quite fond of my curvy ass and my nice, hot pussy, but when it comes to foreplay it?s my tits that he always gives the most attention.

Sandee Westgate has a new boyfriend. Her boyfriend has an adult son who just got in the night before and Sandee decides the best way to introduce herself is to head on over to his room in her sexiest lingerie and give him a morning blowjob . Of course her boyfriend's son is surprised to wake up to a hot women sucking on his cock, specially after he finds out that it's his dad's new girlfriend. Sandee really needs younger cock though and as soon as she pops her tits out her boyfriend's son calms all his fears about fucking his dad's hot girlfriend.

Playboy.com is on set with Victoria James to shoot her exclusive pictorial. Get to know more about Victoria James by watching our behind the scenes footage and the complete nude version available exclusively on Playb?

Kelly Divine is jumping rope out by the pool. Her big ass is nice and bouncing and her boyfriend's friend notices. He notices more than her ass, he also notices her big tits. Well Kelly's boyfriend is out and since his friend is over to use the pool she decides to be a good host and join him...naked. She welcomes her boyfriend's friend to use more than the pool, she invites him to use her pussy too. You don't have to tell him twice. His pants are soon off and he's fucking Kelly on every piece of outdoor furniture there is.

She's busty, brainy, brawny and just plain beautiful! 36DD LaTasha Marzolla, Playboy's Model of the Year from 2004 and a world-class competitive kick-boxer is back in another hot and sexy set for PinupFiles/PinupGlam!

Samantha Bentley flew a long way to finally see her internet boyfriend in person. She's so excited, although she notices that he looks a little different in person than on camera. That doesn't matter to her. She's super horny and has been wanting to fuck him for so long that she strips off her clothes and has him pound her pussy within moments of arriving at his place. It turns out, she was fucking the wrong guy all along. She actually ended up fucking her boyfriend's roommate. Seems like things have a tendency of getting misinterpreted when you're horny and ready to fuck!

Playboy.com is on set with Ana Cheri to shoot her exclusive pictorial. Get to know more about Ana Cheri by watching our behind the scenes footage and the complete nude version available exclusively on Playboy Plus. W?

Allie Haze convinced her boyfriend to sell his house and move to Napa. Her boyfriend's son is upset because that means he will have no where to live. Since he has nothing left to lose he starts making out with his Allie because it's something he's always wanted to do. Seems like Allie has been wanting to do this as well because they end up having a farewell fuck before she moves to Napa.

Playboy Plus is on set with Hillary Fisher to shoot her exclusive pictorial. Get to know more about Hillary Fisher by watching our behind the scenes footage and the complete nude version available exclusively on Play?

Johnny came over to Ashely's place to plan for her boyfriend's birthday party. Johnny has the idea of getting some strippers but, Ashley is definitely not going to let that happen. Johnny starts flirting with Ashley and she tell him to back off. He lets her in on a little secret that her boyfriend beat Johnny to the punch of asking her out. Ashley tells him that she wanted Johnny to ask her out that day too. Johnny uses this to blackmail her into snagging a kiss except that this turn into Ashley taking it on the kitchen counter, up to the bedroom and Johnny's load right on her pussy.

Playboy Plus is on set with Mikaela James to shoot her exclusive pictorial. Get to know more about Mikaela James by watching our behind the scenes footage and the complete nude version available exclusively on Playbo?

Bridgette goes upstairs to "check" on her boyfriend's son Richie all the while trying to flaunt herself hoping he wakes up to it. Bridgette gives him a nudge to wake him up and explains that she's up there because she knows he is afraid of the dark and saw his light on, at least that's what his dad told her. Bridgette thinks Richie will be better off being up there with him and hops onto his bed He questions her actions and she reveals why she's really up there by putting her big tits right in his face! Bridgette is lonely, horny, and wanting to be fucked while Richie's dad is out of town. Richie facing no options other than to fuck this beautiful blonde big tit Latina and he finishes it off by dropping his load in her mouth.

Ashley Fires is mistaken for the help by her boyfriend's son, Preston. Preston always fucks the help, so he can't wait to get his hands on Ashley. When he finally finds out that Ashley is his dad's new girlfriend he backs off, but Ashley wants Preston as much as he wanted her. Ashley always gets what she wants and right now she wants Preston. Ashley sucks and rides Preston's cock before letting him cum all over her mouth and face.

Jynx Maze is upset that her boyfriend's son always has girls over but never has the nerve to do anything with them. After she scares away his new girlfriend Jynx decides to have a heart to heart with him and prepare him for a sexually active lifestyle. As always, safety first. She pulls out a condom and has him put it on. With that out of the way she's ready to show him something a little more fun, like how to properly fuck a girl. She lets him use her pussy as practice and saves his cum filled condom as a present.

Playboy.com is on set with Megan Elizabeth to shoot her exclusive pictorial. Get to know more about Megan Elizabeth by watching our behind the scenes footage and the complete nude version available exclusively on Pla?

Allison Moore is helping her friend's boyfriend tidy up the house a little. Allison is curious though why he would call her to help when it's not too dirty to begin with. Well, what he really needed Allison there for is for support, both emotionally and sexually. Allison is more than willing to provide him all the sexual support he needs.

Tasha Reign is starting a new business and her boyfriend's son, Seth, is helping out by doing some construction work on it. Tasha stops by to check on him and while there she confesses that while Seth's dad is great at taking care of most issues he is slacks in the bedroom. Tasha hasn't been laid in a while and since her man can't give it to her she decides that his son might be a fitting substitute. Tasha seduces Seth and he fucks her in a way his dad never could.

Playboy.com is on set with Amelia Talon to shoot her exclusive pictorial. Get to know more about Amelia Talon by watching our behind the scenes footage and the complete nude version available exclusively on Playboy?

Playboy Plus is on set with Deanna Brooks to shoot her exclusive pictorial. Get to know more about Deanna Brooks by watching our behind the scenes footage and the complete nude version available exclusively on Playbo?

Lovely Miss September returns once again in another scorchingly hot new photo set and boy does she ever make a statement with this one, she gets herself wrapped into a very tiny shimmer bikini and gets herself all oiled up and shiny.

Playboy Plus is on set with Lexi Ray to shoot her exclusive pictorial. Get to know more about Lexi Ray by watching our behind the scenes footage and the complete nude version available exclusively on Playboy Plus. Wa?

Keisha Grey finds out that she's her boyfriend's side bitch. She finds out that the dude he's fucking is actually married so she shows up to the dude's house where she finds her dude's son, Johnny. Keisha decides to fuck Johnny in order to get back at her boyfriend and Johnny is a-ok with that.

Playboy Plus is on set with Danielle Gamba to shoot her exclusive pictorial. Get to know more about Danielle Gamba by watching our behind the scenes footage and the complete nude version available exclusively on Play?

Playboy Plus is on set with Tess Taylor Arlington to shoot her exclusive pictorial. Get to know more about Tess Taylor Arlington by watching our behind the scenes footage and the complete nude version available exclu?

"""All my friends see me as just one of the guys,"" Michelle Lin told us. ""But at the same time, I'm just a regular girl. I could be in a T-shirt and jeans hanging out with the boys one day, and be a total glam girl the?"

Playboy.com is on set with Rebecca Lynn to shoot her exclusive pictorial. Get to know more about Rebecca Lynn by watching our behind the scenes footage and the complete nude version available exclusively on Playbo?

Penny Pax was locked out of her boyfriend's house so she went over to the nearest neighbor to use their phone. While there, her blanket slips off and reveals that she has really sexy lingerie on. She was going to surprise her boyfriend with it when she was locked out. The neighbor is a little taken back and asks her to put her blanket back on since he is a married man and his wife wouldn't appreciate it, but since his wife isn't home Penny decides to keep it off and show the neighbor exactly what she planned on doing with her boyfriend. She drops to her knees and sucks his cock before taking it all over his living room.

Playboy Plus is on set with Kat Kohls to shoot her exclusive pictorial. Get to know more about Kat Kohls by watching our behind the scenes footage and the complete nude version available exclusively on Playboy Plus.?

Playboy Plus is on set with Kimberly Holland to shoot her exclusive pictorial. Get to know more about Kimberly Holland by watching our behind the scenes footage and the complete nude version available exclusively on?

Playboy Plus is on set with Linsey René to shoot her exclusive pictorial. Get to know more about Linsey René by watching our behind the scenes footage and the complete nude version available exclusively on Playboy Pl?

Playboy Plus is on set with Aryka Lynne to shoot her exclusive pictorial. Get to know more about Aryka Lynne by watching our behind the scenes footage and the complete nude version available exclusively on Playboy Pl?

Trinity St. Clair is lounging by the pool trying to get a tan before her boyfriend gets back in town when all of a sudden her boyfriend's friend, Johnny, sneaks up on her and starts soaking her with a water gun. Trinity soaks him back, but now she needs help re-applying lotion so she gets Johnny to help out. Johnny must have magic hands because it starts turning Trinity on. She forgets all about her boyfriend and starts riding Johnny's cock.

Playboy Plus is on set with Amanda Hanshaw to shoot her exclusive pictorial. Get to know more about Amanda Hanshaw by watching our behind the scenes footage and the complete nude version available exclusively on Play?

"""I'm not just some chick,"" declares this aspiring nurse and model. ""I'm a sexy girl who's not afraid to get her hands dirty or break a nail!"" While you may get the impression that Victoria is a tomboy, she's very lad?"

Playboy Plus is on set with Deanna Brooks to shoot her exclusive pictorial. Get to know more about Deanna Brooks by watching our behind the scenes footage and the complete nude version available exclusively on Playbo?

Playboy Plus is on set with Melissa Puente to shoot her exclusive pictorial. Get to know more about Melissa Puente by watching our behind the scenes footage and the complete nude version available exclusively on Play?

Playboy Plus is on set with Christi Taylor to shoot her exclusive pictorial. Get to know more about Christi Taylor by watching our behind the scenes footage and the complete nude version available exclusively on Play?

Playboy.com is on set with Dani Mathers to shoot her exclusive pictorial. Get to know more about Dani Mathers by watching our behind the scenes footage and the complete nude version available exclusively on Playboy P?

Bibi is Raquel's babysitter and the girlfriend of Raquel's son's best friend. As the two are having small talk about Raquel's night out with her girls, her boyfriend Preston comes into the room. It's been a while since Raquel has seen him and wanted to catch up. She asks how long they have been going out and then cuts to the juicy stuff by asking if they are sexually active. Bibi feels awkward about the situation and Raquel goes even further by asking if Bibi is good at giving blowjobs. She even further tips the scale by asking to show her how she does it! Bibi reluctantly agrees and starts giving a horrible blowjob. Raquel steps in to show Bibi how a proper blowjob is suppose to be done with Preston's permission of course. This somehow turns into the best day of Preston's life, a threesome with his girlfriend and friend's mom.

Playboy Plus is on set with Tracey Ly to shoot her exclusive pictorial. Get to know more about Tracey Ly by watching our behind the scenes footage and the complete nude version available exclusively on Playboy Plus.?

Playboy Plus is on set with Ashley Smith to shoot her exclusive pictorial. Get to know more about Ashley Smith by watching our behind the scenes footage and the complete nude version available exclusively on Playboy?

Playboy Plus is on set with Deanna Brooks to shoot her exclusive pictorial. Get to know more about Deanna Brooks by watching our behind the scenes footage and the complete nude version available exclusively on Playbo?

Playboy Plus is on set with Megan Elizabeth to shoot her exclusive pictorial. Get to know more about Megan Elizabeth by watching our behind the scenes footage and the complete nude version available exclusively on Pl?

Playboy Plus is on set with Sarah and Rachel Campbell to shoot her exclusive pictorial. Get to know more about Sarah and Rachel Campbell by watching our behind the scenes footage and the complete nude version availab?

Playboy Plus is on set with Adrianna Kroplewska to shoot her exclusive pictorial. Get to know more about Adrianna Kroplewska by watching our behind the scenes footage and the complete nude version available exclusive?

Hot redhead Monique Alexander has always wanted to be on TV. Luckily her boyfriend's best friend, Johnny, is a big time producer and he has a part in his new show. Monique stops by to discuss why she would be qualified for the part. Johnny just doesn't see it in her, he doesn't think she would fit the role. That is, unless, she fits his dick in her wet pussy. Monique runs out of the house at this suggestion, but she realizes that this is Hollywood and she's going to have to fuck a few dicks to get a head, so she runs right back in and on to Johnny's cock.

"You may recognize the Satterfield triplets from Hef's online party page photos. ""We loved the Playboy Mansion,"" says spokes-sister Sarah. ""We never wanted to leave!"" When we asked the threesome if they'd like to pose?"

Playboy Plus is on set with Heidi Wheeler to shoot her exclusive pictorial. Get to know more about Heidi Wheeler by watching our behind the scenes footage and the complete nude version available exclusively on Playbo?